Triethylamine → 3-[3-Oxo-7-(3-phenyl-prop-1-ynyl)-2H-6-azaisoquinolin-2-ylmethyl]benzonitrile

HRID 488777Notes

Reaction equation

HRID 488777 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][N:8]([CH2:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])[C:7](=[O:21])[CH:6]=2.[C:22]1([CH2:28][C:29]#[CH:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>CN(C)C=O.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:21]=[C:7]1[CH:6]=[C:5]2[C:10]([CH:11]=[C:2]([C:30]#[C:29][CH2:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:3]=[CH:4]2)=[CH:9][N:8]1[CH2:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 575753BenzylacetyleneHCID 222682323-(7-bromo-3-oxo-2H-6-azaisoquinolin-2-ylmethyl)benzonitrile

Product 1

HCID 222682423-[3-Oxo-7-(3-phenyl-prop-1-ynyl)-2H-6-azaisoquinolin-2-ylmethyl]benzonitrile

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The coupling of 3-(7-bromo-3-oxo-2H-6-azaisoquinolin-2-ylmethyl)benzonitrile (0.85 g, 2.51 mmol) with 3-phenyl-1-propyne (0.78 mL, 6.3 mmol) using triethylamine (0.70 mL, 5.0 mmol), CuI (0.034 g, 0.18 mmol), and Pd(Ph3P)4 (0.20 g, 0. 17 mmol) in dimethylformamide is carried out as described in Example 1, Step (2). Purification is carried out on a silica gel column eluted with hexanes/ethyl acetate 3:1 to give the desired product.

Workup

  1. customPurification
  2. washeluted with hexanes/ethyl acetate 3:1

Sources & evidence

ORD record
ord-7be664eeb56046b0858dc0dbdfac00ed
Source dataset
uspto-grants-2005_12
Patent number
US06974822B2

Reaction notes

Loading…